Organohypervalent Iodine Reagents in the Synthesis of Bioactive Heterocycles

Oxidative Heterocycle Formation Using Hypervalent Iodine(III) Reagents

“…In 2010, Fan and coauthors [46] reported a PhIOmediated oxidative cyclization of substrate 49, a Michael adduct of 2-aminomalonates with chalcones, to afford highly functionalized azetidines 50 with high diastereoselectivity (>95:5) (Scheme 11 (2)). The protocol was successfully adopted for the synthesis of biologically and medicinally important oxetanes [47].…”

“…The omnipresence of heterocyclic compounds in many natural products and pharmaceutical agents warrants the development of efficient strategies for their synthesis. In this regard, hypervalent iodine chemistry has emerged as an elegant and powerful tool for the construction of a plethora of bioactive heterocyclic compounds and natural products [1,2]. Recent decades have witnessed a great expansion and significant popularity of hypervalent iodine chemistry because of the ready accessibility, reduced toxicity, high reactivity, impressive functional group tolerance, and environmentally benign nature of hypervalent iodine reagents.…”

Trifluoromethylnitrone: a versatile building block for synthesizing trifluoromethyl-containing heterocyclic compounds

“…When reacting with 2,4-dinitrophenylhydrazine (2,4-DNP, 6), it generates the 2,4-DNP derivative of trifluoroacetaldehyde (7). In the presence of LiAlH 4 (8), it transforms into hydroxylamines, CF 3 CH 2 N(OH) CMe 3 (9), and in the presence of EtMgI (10), into CF 3 CHEtN (OH)CMe 3 (11). Interestingly, it undergoes photoisomerization into the CF 3 CONHCMe 3 amide (12).…”

“…Trifluoromethylated aromatic compounds are commonly present in various pharmaceuticals, agrochemicals, and organic materials. 11 Trifluoromethyl-containing heterocycles including isoxazolidines, dihydroisoxazoles, pyrazoles, and pyridines are found in many bioactive molecules (Fig. 1).…”

Selective Synthesis using ETFBO: A New Strategy for the Preparation of Hexahydro‐1H‐pyrrolo[1,2‐c]imidazol‐1‐one.

“…[6] The introduction of a trifluoromethyl group modulates the physicochemical properties of molecules, which can improve their lipophilicity and stability. [7] Furthermore, the increasing use of fluorinated compounds in life science products constitutes a driving force in the development of regio-and stereoselective routes for the introduction of trifluoromethyl groups into aliphatic, as well as aromatic systems. [8] There are several mechanisms that facilitate the incorporation of a fluorinated group into an organic molecule and the best choice depends on the starting material.…”